Synthesis and Anticonvulsant Activity of Some Alkyl Esters of 6-Chloro-2-sulfamoylbenzoic Acid
1965; Elsevier BV; Volume: 54; Issue: 9 Linguagem: Inglês
10.1002/jps.2600540908
ISSN1520-6017
Autores Tópico(s)Chemical Reaction Mechanisms
ResumoThe application of the Rule of Six for the estimation of steric effects to a series of alkyl esters of 4-amino-2-sulfamoylbenzoic acid possessing pronounced anticonvulsant activity shows the highly hindered isopropyl and sec-butyl esters to be much more potent than the less hindered methyl, ethyl, and n-propyl compounds. In order to provide further information concerning steric factors and anticonvulsant properties, four alkyl 6-chloro-2-sulfamoylbenzoates, which contain the chlorine atom in the shielding position adjacent to the alkoxycarbonyl group, were synthesized: the methyl, ethyl, n-propyl, and isopropyl esters. Preliminary pharmacological results indicate that the isopropyl 6-chloro-2-sulfamoylbenzoate produces strong antielectroshock effects in mice which are quite specific, with no other CNS activity except at high doses in the gross observations. The application of the Rule of Six for the estimation of steric effects to a series of alkyl esters of 4-amino-2-sulfamoylbenzoic acid possessing pronounced anticonvulsant activity shows the highly hindered isopropyl and sec-butyl esters to be much more potent than the less hindered methyl, ethyl, and n-propyl compounds. In order to provide further information concerning steric factors and anticonvulsant properties, four alkyl 6-chloro-2-sulfamoylbenzoates, which contain the chlorine atom in the shielding position adjacent to the alkoxycarbonyl group, were synthesized: the methyl, ethyl, n-propyl, and isopropyl esters. Preliminary pharmacological results indicate that the isopropyl 6-chloro-2-sulfamoylbenzoate produces strong antielectroshock effects in mice which are quite specific, with no other CNS activity except at high doses in the gross observations.
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